From the Magazine

How Jon Stewart Took Over The Daily Show and Revolutionized Late-Night TV: An Oral History

When Jon Stewart arrived at The Daily Show in 1999, he inherited a modest cable success—and a staff that wanted him to leave it alone. In an adaptation from The Daily Show (The Book), Chris Smith gets Stewart, Stephen Colbert, Steve Carell, and others to talk about the battles of that first year, and how the show found its radical voice.

My wildest dream for The Daily Show when I started was “This will be
fun. Hopefully we’ll do it well.” Success for me would’ve been feeling
like I figured it out. That I got to express the things I wanted to. It
was never “I want this to be a cultural touchstone . . . but only
for a very small portion of America.” And I was hoping to stay on TV
longer than nine months this time.

The Daily Show premiered on Comedy Central on July 22, 1996, at 11:30
P.M. The format loosely tracked that of a conventional newscast: five or
so opening minutes called “Headlines,” read by former ESPN anchor
Craig Kilborn, followed by “Other News,” then usually a pre-taped
“field piece” with a correspondent, and finishing up with Kilborn
interviewing an actor or a musician.

Some segments played off the hard news of the day, like the presidential
contest between Bob Dole and Bill Clinton. “There was more of a
pop-culture-and-lifestyle component only because what we were
satirizing—particularly local news—was doing a lot of that stuff,”
co-creator Lizz Winstead says. “We would make fun of the conventions of
news. Like when TV reporters talk, how do you create drama in a story
that doesn’t exist?”

The day-to-day creative process of the first few years of The Daily Show
centered on Winstead, fellow co-creator Madeleine Smithberg, and the
writing staff. “My first day on the job,” Winstead says, “I have to
pull the writers into my office and say, ‘Guys, you can’t have your
mushroom dealer come up to the office.’ ” Kilborn came up with the
signature “Five Questions” conceit for guest interviews, but otherwise
largely read from the script.

In November 1996, Comedy Central’s executives moved The Daily Show to 11
P.M., to replace Bill Maher’s Politically Incorrect, which had jumped to
ABC, but also to counter-program the late local news.

Kilborn’s Daily Show would peak at a nightly average of 357,000, yet
Kilborn’s audience was growing, and the show was generating critical
buzz. Perhaps more important than the chatter was the fact that it was
indeed reaching the younger male viewers Comedy Central president Doug
Herzog had targeted in the first place. The combination caught the
attention of CBS, and in 1998 it offered Kilborn the slot following Late
Night with David Letterman, at 12:30 A.M.

“He starts to get a little heat, we’re starting to get a little
attention with The Daily Show,” Herzog says, “and then the next thing
you know Kilborn goes and signs with CBS without even telling us.”

Panic, followed by auditions: David Alan Grier, Michael McKean, Greg
Proops, Bill Weir, and Mike Rowe came to the studio and sat in the
host’s chair. Daily Show correspondents Beth Littleford and Stephen
Colbert got tryouts, too. But Herzog and other Comedy Central executives
wondered about a black-leather-jacket-wearing stand-up comic, a guy who
had hosted a short-lived MTV talk show produced by Smithberg. He had
lost out to Conan O’Brien as Letterman’s NBC replacement; he had written
a book of satirical essays; he had played Eve Harrington to Garry
Shandling’s Margo Channing on The Larry Sanders Show; and lately he’d
had some supporting roles in Hollywood rom-coms. Herzog didn’t think the
highly regarded, slightly adrift comedian would be interested in the
job. But, hey, what did he have to lose in buying lunch for Jon Stewart?

After The Jon Stewart Show was canceled, he was . . . not burnt on
being on TV, but he wanted to kind of wet his feet with film. We had
this nice deal with Harvey Weinstein.

JON STEWART: At the time, I was obviously making my mark in such films
as Wishful Thinking and Dancing with Architecture, or Dancing About
. . . Oh, no. They ended up calling it something else. Playing by
Heart, I think it was.

Getting fired from the talk show was the real turning point for me.
Because I thought that, after appearing on Letterman, now I’m a made
man. I thought losing The Jon Stewart Show meant I was an unmade man. I
realized you still have to make your act better. The goal is to produce,
the goal is to make things. So I spent some time writing and performing
on The Larry Sanders Show, and I learned a lot from Garry Shandling.

JUDD APATOW(stand-up comic, writer, director):

Garry had the foresight to write about the talk-show wars and this very
subtle aspect of it, which is you support a young comedian, and slowly
the network likes him more than it likes you, and then that younger guy,
in ways that he understands and might not understand, slowly pushes you
out of your job. Similar to what really happened with Leno and Conan and
Fallon. So there was a moment when Garry was considering continuing The
Larry Sanders Show and changing the name of it to The John Stewart Show,
with an h so it wouldn’t really be Jon. Everyone was excited about it
for a while, but it went away.

JON STEWART:The Daily Show wasn’t necessarily on the radar. I think
they called and said, “Hey, man, would you be interested in talking
about this?”—something along those lines, something as romantic as
that.

JAMES DIXON: I definitely advocated for him to do it. I just said to
him, “You can put this through your prism. You can make it smarter and
different than what it’s been.” Now, I definitely didn’t see the show
becoming the political lightning rod that it evolved into.

In the summer of ‘98, when we announced that Jon was going to take over
The Daily Show, we had a little press conference in the lobby of the old
Comedy Central offices. And Stephen Colbert showed up, as a member of
the press representing The Daily Show, wanting to know why he didn’t get
the job.

STEPHEN COLBERT(correspondent, 1997-2005):

“You told me he wasn’t funny.” That’s what Jon said to Doug Herzog.

MATT LABOV(publicist for Jon Stewart, 1994-2008):

The stakes for Jon were fairly high at that point, because he’s not a
super-young guy anymore, and he’s had shots, and people easily disappear
and go into the woodwork. He didn’t get the Conan job on NBC; he didn’t
get the 12:30 job after Letterman. If this doesn’t work on fucking
cable, then where would Jon have ended up?

JON STEWART: A couple of months before I officially started as host
there was a meeting with the writers and producers. Let’s call that
“Jonny’s surprise party.” I knew that the people working on the
Kilborn show were rightfully proud of it. It had done well. It was not
the sensibility that I thought was right for me, and so when they
approached me for the show, I was pretty clear about the direction I
thought I wanted to take it. Seemed like everybody was on board with
that, and so this was my first chance to meet with all the people who, I
had been told, were so excited about that. So excited. They’re so happy
you’re here.

And I walked in, and it was a room full of people who, as it turned out,
were annoyed that I had an idea about where I wanted to go, who thought
that I was going to MTV it up. I was told, “This isn’t about bands. We
do a real show here.” I just sat there like “Oh, fuck.” It felt a
little bit like “Wow, none of this was in the brochure. The brochure
said that this was oceanfront property.”

JAMES DIXON: I had to talk Jon down. Not from a tree—from a
skyscraper. Because they basically said to him, “Welcome aboard. This
is how we do shit here. Grab a chair.” It was bullshit.

PAUL RUDD(actor):

Technically I was Jon’s first Daily Show guest interview. I went to the
University of Kansas, and my roommate, Stewart Bailey, became a segment
producer who was with the show from the very beginning. I’d been on
Kilborn’s Daily Show. When Jon replaced Craig, they wanted to do a test
show so Jon could get used to the format.

Stewart made his debut on Monday, January 11, 1999. His first joke was
that Kilborn was “on assignment in Kuala Lumpur.” His first headline,
“The Final Blow,” was about the Senate impeachment trial of President
Bill Clinton. His first guest was Michael J. Fox, then starring on ABC’s
Spin City. But Stewart looked, for the first months, very much the guest
himself. Other than a new couch and desktop—and blue script pages for
Stewart to scribble on portentously, replacing Kilborn’s white
paper—the set design was largely unchanged. The theme song, Bob
Mould’s “Dog on Fire,” was the same. And Stewart’s suits were so
ill-fitting that they looked like they were inherited from his much
taller predecessor.

During the Kilborn era, it was about “How can we seem like we’ve gone
too far?” With Jon, we went from creating the news—creating funny
spoof headlines—to making fun of the news. That was a big change.

MO ROCCA(correspondent, 1998-2003):

Shortly after Jon arrived, we had done a bit about Dana Plato dying, and
Jon felt bad about delivering a joke when the end of her life had been
so pathetic. We had a meeting where he said he had resolved that the
show needed to have a point of view and couldn’t just be the kid at the
back of the classroom throwing spitballs in all directions. I remember
people trading the kind of glances that said, “Oh shit, this is going
to be a disaster.”

JON STEWART: To be fair to the writers who stayed from Kilborn’s show,
they had a successful thing going. They thought of it as a continuation
of their show. I thought it was a new show. To me it wasn’t edgy or
provocative to just take napalm to a bush for no reason. You wanted it
to be pointed, purposeful, intentional, surgical.

I felt like I walked in there with a very open “O.K., so this will be
great,” and it was “Hey, motherfucker, you came here to kill a baby.”

KENT JONES(writer, 1996-2001):

Well, I would not agree with that. I don’t remember any of this being as
hostile as it has been portrayed. I just don’t.

MADELEINE SMITHBERG(co-creator; executive producer, 1996-2002):

Because of the point of view that had been created by Craig Kilborn
sitting in the chair, the writers’ role had inflated. Yeah, they were
spoiled rotten, because almost every show in late night is talent
driven. They got too big for their britches.

JON STEWART: Six or eight weeks in, the writers called me into their
office. They’re like, “You can’t change our jokes anymore.” I didn’t
know what to say.

So after a weekend of pacing and smoking and having tremendous
Lincoln-Douglas debates on the couch by myself, I went back in, and it
was horrible. I basically told them all to fuck off. “You work for me.
And if you don’t like the direction, O.K. I get that. Don’t work here.”

“THERE WERE POINTS WHERE I THOUGHT . . . I’VE GOT TO LEAVE,” SAYS
STEWART OF THE EARLY TURMOIL.

There were points where I thought, I made the wrong decision. I’ve got
to leave. But I don’t give up very easily. It was open hostility, which
is so enjoyable. It became that sense of “O.K., let’s arm-wrestle.”
This will give you a hint of my personality of grudges.

I didn’t really have a game plan. I knew what I didn’t want. But then
turning it into what you did want was the next scenario, and that was
going to take time, and effort, and accomplices. What I needed most were
accomplices.

BEN KARLIN(head writer, later executive producer, 1999-2006):

I was living in Los Angeles, working with a bunch of guys from The
Onion, selling pilots and doing punch-up on movies. We did a pilot for
Fox called Deadline Now, at about the same time The Daily Show was
launching. We kind of did the exact opposite. We didn’t want to be
winking at the audience. We wanted to play it straight and not really
acknowledge we were a comedy show. We hired actors and went about trying
to produce a news show that was very much in the spirit of the Onion
newspaper. And, frankly, we were quite scornful of the Kilborn Daily
Show.

Our template host, when we’d come up with show ideas, was always Jon
Stewart. We loved Jon Stewart. So when it was announced that Jon was
taking over The Daily Show, our little comedy-snob nerd group thought it
was a bad move. For him. Comedy Central was still pretty second-tier,
and that might even be nice. And Jon was the Letterman heir apparent.

I got a call from my agent saying, “Listen, Jon is looking for a new
head writer, loves The Onion, has heard that you’re kind of the de facto
leader of the Onion guys’ group out in L.A. Would you be willing to come
out to New York and meet with them?”

JON STEWART: I really liked his sensibility. Ben seemed to be concerned
with hypocrisy and the silly façades of politics. He seemed to know
where the absurdity was, and that was an important change in focus for
what we wanted to do. There’s also a certain steeped-in-neurosis bathos
that probably was a rhythm that we both clicked on. That similar Jewie
Jewerman from Jewville.

The big thing was to find somebody who had thoughts, who cared, who had
an opinion. Part of what The Onion is, and part of what Ben was steeped
in, was the idea of deconstruction as your first step of re-creation. So
Ben was a natural fit, although he had not had the TV experience.

BEN KARLIN: I was friendly with Bob Odenkirk and David Cross. They were
kind of like the grand Pooh-Bahs of the alternative-comedy scene in
L.A.—Sarah Silverman, Janeane Garofalo, Patton Oswalt. It was that
whole wave of comics. Bob and David said The Daily Show sounded like a
great opportunity. So I sublet my apartment, sold my Harley, found
someone to take my dog for a while, and came to New York with three
duffel bags.

JON STEWART: Ben walked into a buzz saw.

BEN KARLIN: I’m not going to talk shit about anybody. But the staff had
its allegiances, and the things that they liked to do, and the way they
liked to do it. Now you’ve got this guy, Jon, who is a writer, who has a
strong point of view.

LIZZ WINSTEAD(co-creator; head writer, correspondent, 1996-1998):

As much as I loved the original writers, I created some little monsters.
Once Jon realized he needed to take charge, you can’t afford to have
people who are not in the Jon Stewart business. And so there’s a bit of
Kool-Aid drinking that has to take place.

Karlin arrived as head writer in April 1999 and quickly formed a
complementary duo with Stewart. Karlin pushed for a higher quotient of
righteous anger in The Daily Show’s jokes; Stewart had an innate sense
of what would get big laughs.

BEN KARLIN: We were very kindred spirits, with very similar points of
view, and my critique of the show was very much in line with his
problems with the show: Why are we going after these helpless targets?
Maybe we should focus the power of this kind of big news show on things
that are actually newsworthy, rather than just look through the paper
for what seems funny.

Clashes, pitting Stewart and Karlin against some of the holdover Kilborn
writers, would flare for the next year, with one confrontation—which
became known inside the show as “the fuck-you meeting”—being leaked
to the New York Post’s “Page Six.”

JON STEWART: I think that was the meeting where I said, “You’re not a
group. You’re not a unit. You’re not ‘the writers.’ You’re individual
writers that have been hired, and you will be judged within that.” It
was just an attempt to reclaim some semblance of order. It was an
absolute flat-out power struggle, but one that I felt blindsided by.

BEN KARLIN: At one point during the battle for the heart and soul of the
show, one of the writers snuck into Madeleine’s office and replaced some
of the items on the board that tracks the stories we’re doing with
personal insults. Some of them were about me; some were about other
people. It was the most juvenile thing in the world. Jon and I used to
have this thing: crazy out, sane in. We wanted to try to build a show of
smart, funny, reasonable people with a similar vision who were hard
workers.

An enormous step in that direction was Karlin’s first addition to the
writing staff: a dizzyingly fast-thinking, cheerfully caustic
27-year-old who would become a major figure in the creative life of The
Daily Show.

DAVID JAVERBAUM(writer, later executive producer, 1999-2010):

I’d gone to Harvard and written for the Lampoon and Hasty Pudding, then
I went to graduate school for musical-theater composition, at N.Y.U.
It’s arguably the most useless master’s degree even by master’s-degree
standards. I had a lot of creative things I was interested in, but I had
no idea what I wanted to do. I was temping for three years at law firms
and Merrill Lynch.

I knew Ben Karlin from a teen tour that we were on together, the thing
where Jewish middle-class kids go around the country and pretend to
rough it for six weeks. Ben, after college at Wisconsin, wound up
working at The Onion, and he said, “Do you want to contribute?” So I
began writing a lot of Onion headlines and some articles, and I had the
idea for the book Our Dumb Century.

Then I spent a year at Letterman as a writer, and I hated that. Not the
people, per se, but it all comes from the top down, and Letterman, even
at that point, which was ‘98 to ‘99, was just a detached, aloof figure
who would stay there for, like, 13 hours a day for no reason. And I
quit. I was making six figures. I’d never made the upper half of five
before, but it just was not worth it. It was crushing my soul.

Ben was hired as the head writer for The Daily Show, and once again he
called me and said, “Are you interested in writing?” So I owe Ben for
both of those opportunities. I think I was Ben’s first writing hire, in
July 1999.

BEN KARLIN: D.J. has genius-like qualities, almost to the point
where—it’s not Asperger-y, because he’s a funny, normal guy. But the
way he can hold information, the speed with which his mind works, it’s
almost like he’s got a broken brain that works really well in this way.
I’ve known him since he was 16 years old. He always was like this.

Usually in a writers’ room you know that this guy is my joke guy, that
one is my story guy, that’s my structure person. And D.J. has the
ability to pitch individual jokes that are funny; he can come up with
overarching structures that are funny; he can take over someone’s script
and make it better.

In Karlin, and now Javerbaum, Stewart had hired invaluable off-camera
allies. But he quickly recognized that he had inherited an indispensable
on-camera co-conspirator. Stephen Colbert had a subversive streak that
was greatly abetted by the fact that he looked like a trustworthy
middle-American insurance salesman.

STEPHEN COLBERT: It was a complete happy accident that I ended up at The
Daily Show. I had been working for ABC at The Dana Carvey Show in 1996.
That show got canceled, my wife wasn’t working, and we had a baby. I
desperately needed a job. Someone from the entertainment division
recommended to the news division that if they were looking for somebody
who was funny but looked really straight, for a correspondent for Good
Morning America, that they should consider me. They hired me. I did
exactly two reports. Only one of which ever made it to air.

After those two reports, I pitched 20 stories in a row that got shot
down. At the same time, my agent, James Dixon, who also represented
Madeleine Smithberg, said, “You should meet with Madeleine. She’s doing
this other show, and I bet that they would do those stories.” They had
me on for a trial basis, and for the next nine months I worked at The
Daily Show occasionally, during Craig Kilborn’s second year. But it was
totally a day job. I never expected to stay, because I did sketch comedy
and I wrote, and I really didn’t think that The Daily Show was going to
go anyplace.

JON STEWART: The first bit Stephen did on the show after I arrived, I
think it was something about baby-back ribs. You could just feel: “This
guy knows how to perform in a scene, is present, has an ease with
language.” The key then was “What do we do with that?”

STEPHEN COLBERT: I don’t really know why Jon and I worked together so
well. It’s hard to quantify, but it happened very early. When Jon first
got there, he had a rough ride with some of the people who had worked
with Craig. But I immediately knew he was a guy I should listen to. I
saw how thoughtful he wanted to be about political comedy and how he
invited us to have our own thoughts, invest the jokes with our own
beliefs. And maybe he thought he could trust me.

Changing the lineup of correspondents and contributors, the on-air faces
of the show, was crucial, if less contentious. A. Whitney Brown and
Brian Unger left when Kilborn did; Colbert, Rocca, Beth Littleford,
Frank DeCaro, and Stacey Grenrock Woods stayed on. Stewart’s first
correspondent addition was Vance DeGeneres. Then Colbert helped recruit
another major talent.

STEVE CARELL(correspondent, 1999-2003):

I got a call from Stephen Colbert. He and I were on The Dana Carvey Show
together in the spring of 1996, and one of the sketches that we did was
called “Waiters Who Are Nauseated by Food.” And Madeleine Smithberg,
who had hired Stephen onto The Daily Show, saw that and asked who I
was—asked Stephen—and then Stephen called me and said, “Would you
be interested maybe in doing a field piece?” And then Madeleine called
and followed up and asked if I’d do a field piece out here in Los
Angeles. Nancy [Walls Carell] and I were living out here at the
time, and I had a holding deal with ABC. So we were just watching a lot
of the Game Show Network.

We decided to stage the field piece right underneath the HOLLYWOOD sign,
up in the Hills, and that I was going to do the walk-and-talk as I was
essentially walking up the side of a mountain, and obviously play up the
fact that I was really out of shape, that it was a very bad
correspondent to have chosen for a walk-and-talk.

Apparently Madeleine really liked that moment within the piece and
thought that that was a good choice. They asked if I’d move out to New
York and be a regular on The Daily Show.

No one was really familiar with this show. My agent didn’t see it as a
positive step in my career. Let’s put it that way. They just saw it as a
little nothing cable show. A job, but nothing that was going to amount
to much. Jon had just become the host about six months before.

JON STEWART: Carell, I knew very little about him. These guys didn’t
come from stand-up. I knew stand-ups. I knew Dave Attell, I knew Lewis
Black. I did not know Vance, Mo, Steve, Stephen.

BEN KARLIN: So much of the writing of The Daily Show actually comes down
to brainstorming and coming up with the big-picture ideas. Once we
started realizing what an incredible tool Carell and Colbert were, we
said we’ve got to bring more of that into the studio. Let’s not just see
them once a week or once every two weeks in a field piece. Let’s get
both those guys on the show several times a week in one form or another.
They’re too talented.

What Stewart and his colleagues could not have known was that they had
arrived at the perfect moment, with the media and political worlds on
the cusp of upheaval. When Stewart first sat behind the fake anchor
desk, the anchors of the real news were still a trio of white male
eminences: Tom Brokaw at NBC, Peter Jennings at ABC, and Dan Rather at
CBS. But the network news hegemony had been rattled by the arrival of
CNN, and especially by its coverage of the 1990 Gulf War. Now Fox News
and MSNBC—both launched, coincidentally, within months of The Daily
Show’s 1996 debut—were rapidly expanding their footprints on cable
systems. Soon the Internet would flatten the traditional TV news
industry. And a wised-up, postmodern generation of viewers was hungry
for what The Daily Show would soon deliver.

The turn of the century was also a boom time for network newsmagazines.
NBC was airing Dateline five nights a week. ABC had 20/20 and Primetime;
CBS had 48 Hours. Syndicated shows including Inside Edition added an
even cheesier, tabloid flair to the genre. The TV-newsmagazine
formula—leaning heavily on sensationalized crime stories, breathless
celebrity profiles, and consumer-product scares—was ripe for parody.
As were the self-serious anchor-reporter stars of TV newsmagazines: the
style of The Daily Show’s correspondents drew special inspiration from
the overinflated gravitas of Dateline’s Stone Phillips.

MADELEINE SMITHBERG: I always say that Stone Phillips deserves a
“created by” credit for The Daily Show, because I was obsessed with
the guy, and we studied him.

Colbert will tell you his character for years was just Stone Phillips.

In the Kilborn era, field-department pieces frequently featured obscure
eccentrics—say, a man who pulled his own teeth and replaced them with
driveway gravel. Those kinds of bits didn’t go away immediately under
Stewart.

I produced a field piece, with Stacey Grenrock Woods as the
correspondent, about a guy, Alexander P., who had been a rock star in
Ukraine and came here and was now a waiter in a hotel restaurant in
Grand Rapids, Michigan. This piece may well have been in the works
before Jon arrived. But it airs, and after the show you have a
postmortem. And Jon was not happy. He said, “Your targets are just
wrong. They shouldn’t be people on the fringe. Our targets need to be
the people who have a voice, and that’s politicians, and that’s the
media.”

STACEY GRENROCK WOODS(correspondent, 1998-2003):

I heard Jon was very unhappy with that piece, and I don’t blame him at
all. I didn’t like it, either, but it was given to me. I think it ended
up being a policy-changing piece.

STEVE CARELL: The correspondents had their own little thing going on
with the field pieces. Jon left it up to us in terms of what sort of
characters we were developing.

I saw my character as a former local-news anchor who had been demoted to
reporting on a nondescript cable news show and was a little bitter about
it. Everyone to a certain degree had different variations on blowhard or
idiot reporter. But I mean, let’s face it—we didn’t know what we were
doing.

NANCY WALLS CARELL(correspondent, 1999-2002):

No.

STEVE CARELL: None of us are correspondents. None of us have backgrounds
in journalism.

NANCY WALLS CARELL: Mo was pretty knowledgeable, actually.

STEPHEN COLBERT: There was a very specific way we were supposed to
present ourselves when we set up field pieces: “I’m from The Daily
Show.” “What’s The Daily Show?” “Well, it’s an alternative
news-and-entertainment program.” “What channel is it on?” “Well, I
don’t know what channel it is where you live. Where we live it’s Channel
29.” Anything other than saying the words “Comedy Central.” We were
never allowed to lie, but let’s not advertise we were on Comedy Central,
because not being a famous show was really useful to us in the early
days.

I was the first correspondent to be sued. After a piece ran, a guy
claimed I claimed I was from CNN. I never said that. But if you make a
man comedically look like Hitler and it turns out that he is a retired
lawyer with a lot of time on his hands, you’re going to get sued. That’s
the lesson for today, children.

STEVE CARELL: The field pieces with eccentrics and oddballs, those were
uncomfortable. For all of us. I almost didn’t . . . I won’t say I
almost didn’t do the show, but I had some major reservations about doing
it for exactly that reason, because I didn’t like the idea of making fun
of people only because they were eccentric or different, and . . .

NANCY WALLS CARELL: Duping them.

STEVE CARELL: Yeah. Shooting fish in a barrel is easy. When you go after
someone who is intolerant or racist or has any sort of hateful nature,
that’s a different story. I think that’s fair game. So part of what I
tried to do with my character is put the impetus on myself, the comedic
impetus, that I was the bigger idiot.

During his first year as host Stewart devoted far more energy to
retooling the staff and the process inside the building. But it was the
field department, in a series of excursions to New Hampshire to
“cover” the presidential primaries, that really began pointing
The Daily Show’s tone and point of view in a new direction. Initially
intimidated by the straight political media pack, correspondents Rocca,
Walls Carell, DeGeneres, and Carell played jester.

Stewart with, from left, writers Rich Blomquist, J. R. Havlan, Jason Reich, and Tim Carvell, photographed
by Annie Leibovitz on the Daily Show set in 2004.

Photograph by Annie Leibovitz.

STEVE CARELL: When we went up to the first Republican debate we had our
jackets with “The Daily Show” embroidered on them, and we’re walking
around with microphones. It was terrifying because people didn’t know
that we were fake. So we could get away with a lot of stuff. Bush looked
at us like we were insane.

CINDY McCAIN(wife of Senator John McCain):

All of a sudden there were these guys in these crazy jackets, popping up
at campaign events, and nobody knew who they were. But they were funny.

STEW BAILEY(field producer, later co-executive producer, 1996-2005):

There was a Republican debate in New Hampshire, so we were going to do a
piece from the spin room. And the spin room even then was acknowledged
as the least newsworthy event of all time. Our premise was that it’s
essentially a parlor game, and if that’s the case, let’s really turn it
into a parlor game. I had each of the correspondents asking questions
from Trivial Pursuit to the candidates.

MO ROCCA: All of us were nervous as hell, and so I just went for it:
“Senator McCain, who became the hottest pop star to come out of Iceland
in the mid-1990s?”

__MO ROCCA: __And McCain showed why he almost upended George W. Bush in that
race, because he played along, making this silly face. I remember the
CNN people looking at us like, “O.K., that was funny. But who are you
guys?”

JON STEWART: When we went up to New Hampshire we were under the mistaken
assumption that we had to integrate ourselves with the political media’s
process and become them to parody them. Turns out we didn’t have to do
that. We had thought, Oh, you’re a political reporter on television,
which must mean something. Turns out it doesn’t mean anything. All it
means is that somebody pointed a camera at you and lit it. So that was a
revelation, and not a positive one.

Then, in December 1999, came a breakthrough—a five-minute segment that
pushed past the silly and into the satirical. Carell climbed onto
McCain’s bus and changed the entire trajectory of The Daily Show.

STEW BAILEY: Remember, McCain that year was a huge deal. He won the New
Hampshire primary. That was really his moment. And his big gimmick was
his bus, the Straight Talk Express.

I was supervising in the field department. Our idea was that we were
trying to get on the Straight Talk Express, but we couldn’t. There was a
secondary press bus. If you’re in the rollover bus you just don’t feel
like you matter. So the premise was going to be: if Steve Carell finally
does get on the Straight Talk Express, that means we were at the table
with all the big important players. To get on McCain’s bus was a coup
for us; it meant that somebody was going to allow us to bring our
reindeer games into a legitimate political moment.

CINDY McCAIN: The actual press bus, which was completely different from
ours, was really awful, in fact. Steve Carell was talking about, did we
feed the press, or did we just lock them in the bus? They were pleading
with me—is there any way I can get them on the main bus? They were a
hoot to be around, so John invited them on the Straight Talk Express.

STEW BAILEY: We needed to then have Carell basically ask one question
that is going to get us kicked off. The idea was going to be we had a
brief moment of glory, we asked a question, and then we lost our
privileges.

McCAIN: If I were a tree, I would be a root. [Pause.] What does that
mean?

CARELL: Senator, how do you reconcile the fact that you were one of the
most vocal critics of pork-barrel politics and yet while you were
chairman of the Commerce Committee that committee set a record for
unauthorized appropriations? [Four seconds of silence that feel like
four hours.] I was just kidding! I don’t even know what that means!
[McCain looks at ceiling, shrugs in relief, awkwardly slaps hand to
his own face. Carell shuffles sheepishly down the bus stairs and out the
door, then stands on a highway median.] Oh, they all laughed at my
little question. But two things were abundantly clear. It was the wrong
question to ask, and I was going to be walking.

STEW BAILEY: Carell and Nick McKinney, the producer, had pulled the
question out of Time on the way there, driving to the shoot. Just the
fact that Steve Carell can get those words out of his mouth and that it
sounded like something a smart person would say really threw McCain off.
There was such a delay.

STEVE CARELL: It was really funny because all of McCain’s handlers
. . . you could feel the whole bus tense up. I thought McCain might
just laugh it off, or probably give me some sort of joke response.

BEN KARLIN: I remember seeing it in the editing room. I remember Jon
called me down, and seeing it and thinking, Yeah, this is what we should
be doing. This is the goal. It was one of Carell’s most incredible
moments. He asks McCain a question in a way that no journalists were
talking to the candidates. And it was like, Oh shit, we are able, in
this weird, unintentional way, to add a level of insight to the process
that doesn’t exist. That was really, really exciting. It meets the
standard of being funny; it meets the standard of being relevant.

That was great. I still remember Steve Carell on the bus. I was
certainly aware of Jon and the show early on, and knew they would try to
have some fun with us. I wanted to be funny. I wanted these young people
to know that I’m a guy with a sense of humor. I’m not some dull, dry,
old senator.

BEN KARLIN: That moment, it was the beauty and the weakness of The Daily
Show. You had this incredibly pregnant moment where you forced a
politician to go off-book, and it was uncomfortable, and it was honest.
Then, because of our role as a comedy show, you have to take the air out
of it, and it let McCain off the hook.

STEVE CARELL: Yeah, to press it—we really hadn’t set ourselves up in
that context to start going after him. It was making fun of a gotcha
moment. And I think that a lot of what we do on The Daily Show is making
fun of journalistic tropes, and I think that was one of them.

MO ROCCA: That was the first time we were in The New York Times—in a
news-analysis piece, not the TV column.

JON STEWART: The real revelation for the show, covering the 2000
campaign, was that before everything that happens publicly in politics
there’s a meeting—so what’s that meeting? That’s what’s interesting.
It always struck me as “We’re always covering the wrong thing. We’re
always covering the appearance, but we’re never covering that meeting.”
When you watch that pack of cameras follow a presidential candidate, you
go, “That’s not interesting. What’s interesting is to stand behind them
and watch that,” because then you learn a little bit about the process.

That’s when the idea of deconstructing the process came to the fore of
how we were going to make the show. Before, it was just . . . we were
making jokes. Some of them were insightful; some of them were not. The
show came to exist in the space between what they’re telling you in
public and the meeting that they had where they decided to do it that
way. Seeing that was the aha of “That’s the show.”

CINDY McCAIN: I still have those jackets, by the way. I talked them out
of their big New Hampshire jackets. They were around John so much, and I
finally said, “Look, these jackets are too good. I’ve got to get one
from you, please.” They gave them to me. It’s a great souvenir.